


Jessie for Rent

by FestivalGrey



Series: Jessie for Rent [1]
Category: Pocket Monsters | Pokemon (Anime), Pocket Monsters | Pokemon - All Media Types
Genre: Breast Fucking, Dirty Talk, F/M, I can only imagine what James is up to, Multiple Orgasms, Oral Sex, Rough Sex, Sex for Money, Vaginal Sex
Language: English
Status: Completed
Published: 2018-07-19
Updated: 2018-07-19
Packaged: 2019-06-13 05:45:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,583
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15357543
Author URL: https://archiveofourown.org/users/FestivalGrey/pseuds/FestivalGrey
Summary: You, the reader, are spending a normal day in the world of pokemon, until you spy a Team Rocket member in the alley across the street. When you see a certain something she probably wasn’t intending, your confidence spikes, and things turn interesting for both of you… Commissioned by purpistol over on FA. 18+, Male Reader x Jessie





	Jessie for Rent

The sun warms your skin. It’s the perfect sort of day. Pokemon scurry around near the edges of buildings, pouncing on and playing with each other. You see Meowth stalking Pidgey, Pikachu congregating around electrical outlets, and there are even a few Butterfree winging overhead. It’s the sort of day that makes you glad to be alive.

You’re finishing up your early lunch at your favorite café, enjoying the space they have set aside for eating outdoors. Setting down your fork, you pick up the last of your coffee, savoring its richness as you gulp it down. You put the now-empty cup down with a satisfied sigh. It’s just getting to be that busy time of day when people stroll down the pavement, chasing whatever business they have elsewhere. Pokemon trail after them, sometimes following their masters, sometimes pursuing errands of their own. You settle back to enjoy a spot of people-watching.

The harried crowd shuffles back and forth, to your amusement. As things wind down, you find your eyes drawn to the Pokemon Center across the street. People have been going in and out of it all day long, as to be expected, but now there’s some small sort of activity going on in the alley at its side. Your interest piqued, you lean in closer.

There’s a woman in the alley, and she’s clearly up to something. She’s eying vents on the side of the center, perhaps looking for a way in, and testing drainpipes and other things. Is she scoping out a way into the building? You feel slightly alarmed, especially when she turns to wipe her brow. Her white uniform as a very prominent red letter “R” emblazoned across the front of it, almost guaranteeing she works for the criminal gang Team Rocket. You lean back, deciding not to get involved.

And yet… looking at her, you can’t help but note her attractiveness. Her long, luxurious red-purple hair frames a face with full lips and striking blue eyes. She’s tall—taller than you, slightly—and her figure is divine.

The woman continued her activities, scoping out the exterior of the Pokemon Center, none the wiser to your attention. You sit back and drink in more of her appearance. She has a fit frame that suggests a physically active lifestyle, with curvy breasts and enticingly wide hips. You find yourself growing a little hot the more you stare, your interest piquing. There’s a bulge in your pants growing firmer and firmer.

Her black boots, reaching well past her knees, hug her legs tight and show off their shape. Her thighs swell out a bit where the boots end, alluringly lush, and the black undershirt beneath her white top also clings tightly to the skin, letting her body puff out a bit where the constricting clothing ends. When she reaches up to try and grab at a high-placed vent, you see the dark undershirt’s contours against her breasts, enticingly big and round. The small yet noticeable push from her nipples stand out against the black fabric, and you idly imagine yourself rubbing your thumb across the sensitive nubs, shivering at her imagined cries of pleasure.

Her back is to you again, and you take the time to appreciate her ass as she wiggles it side to side as she frustratedly tries to reach the upper vent. It’s is quite large, you think, and complements the rest of her figure nicely…

Apparently frustrated of trying to jump for the vent, she decides to bend over and grab a box to climb it instead. When she does, her lower skirt rides down, allowing you a peek at her black panties. There’s some sort of writing on them, scrawled in white…

“Rental Mommy $10” is what it says. The implications make your breath hitch and your pants immediately become even less roomy. You wonder if she meant to wear those today. So the Team Rocket member was kinky, huh… you liked that.

And sitting there in the outdoors, the warm sun beating down on your skin and your cock pressing against your pants, you decide to do something daring.

Getting up, you leave money on the table. Then, keeping your eye on the Rocket member, you cross the street and make your way into the quiet alley.

The difference is like night and day. Inside the alley, the air is cool and slightly heavy, and the bustle from the city outside fades away to a distant hum. You spy a couple of wooden pallets leaning against the wall further in; the perfect place to hide should anything come up.

It isn’t until you’re nearly on her that the woman realizes you’re there. She spins around, astonished, before her face sets into a scowl. “What do you want? Don’t you know you’re speaking to Jessie, notorious scoundrel from Team Rocket?” She gestures at the large R on her chest, inadvertently drawing your eyes to her breasts once more. She realizes where your gaze is falling and blushes even more. “ _Well_? G-get out! Or else!”

You simply smirk and pull out a ten-dollar bill. “I understand that you’re open for rent?”

Jessie’s bravado dissipates as she burns a scarlet red. “That’s not—I’m—” She swallows huffily and idly tugs at her skirt. “Now listen, just because I’m wearing—how did you even see—” She knuckles her head in frustration. “I can’t believe it…” she mutters in embarrassment.

You could try to make your case—but you’ve always found that visuals help. Wordlessly, you unbuckle your pants and let them drop. Jessie trails off in a series of astonished sounds as she stares at the tremendous bulge pushing against your briefs. “I… w-whoa…” she says, unable to take her eyes off of it. You can’t help but feel a tiny surge of self-satisfaction.

You proffer the bill to her again. Her eyes trail from the bill to the bulge to the bill. She licks her lips slightly, and trembles with excitement, the movement causing her exposed tummy to shiver.

“W-well then…” she says, her voice tremulous, before she stops. Eying the street outside, she crooks a finger and leads you deeper into the alley, behind the pallets. Back there, no one can see you. When she turns and looks you in the eyes, her hand effortlessly sliding the bill out of you, they smolder with need and delight. “How will mommy satisfy you today?” Her voice is sultry and low.

You waste no time. Holding her shoulders tight, you maneuver her into a low, half-kneeling position so that her chest is even with your cock. Smirking at her, you drop your briefs, allowing your member full reign for the first time. Her eyes alight on it hungrily, her mouth twitching as if she aches to take it in right there, but you have other plans for her.

Swinging your hips low, you angle your cock against her torso, enjoying the sensation of your firm rod against her supple flesh. Jessie’s breath hitches for a moment, but her composure returns soon after. “Mommy’s ready,” she says, her voice smooth.

With that, you swing her hips up and begin fucking her tits right then and there.

Her dark undershirt holds her breasts together tight, squeezing them into each other. The space between is soft and yielding, and the pillowy tits provide a lot of cushioning for your cock. You grunt and begin hammering away, sliding your thick rod in and out, in and out, fucking her tits over and over. The sensation is marvelous—the softness of her breasts coupled with the tightness of them being squeezed together by her undershirt provides the perfect mix of inflexibility and yieldingness.

Despite how tight her undershirt is, your thrusts are so strong that they send her tits bouncing slightly. You can make out her nipples hardening even more than they were before, pushing out as hard nubs against the fabric.

Those aren’t the only signs she’s enjoying it. Jessie’s composure has slipped, moving away from the sultry and confident “mommy” and into that of a young woman grappling with the throes of sexual bliss. Her face is flush with arousal, her eyes unfocused, and her breaths, initially long and deep, have spiraled down into a series of short, excited gasps.

One particularly excited squeal from her accompanies another shift as she begins to shiver with pleasure. She glances down at her chest, blushing even more as she sees your massive cock hammering in and out of her cleavage, and the shivering intensifies.

Seeing her in such a state fills you with pride and vigor, and your increase your pace, fucking her tits harder and harder. Her gasps evolve into lusty grunts and moans, and she shudders even harder as orgasmic bliss takes her. The smell of her arousal hits the air. “C-cum for mommy,” she forces out between grunts and squeals. “B-be a good boy and c-cum for mommy now.”

Dutifully, you slam your cock as far into her cleavage as you can, and grunt as your own orgasm washes over you. You cum all over her boobs and chest, and some of it even spurts out by her neck.

Slipping your cock free, you stumble back and sit down, chest heaving for breath. Jessie is also struggling to regain her wind, leaning against the alley wall, her limbs shaky. You cum gleams on her neck where it landed and she idly wipes it up with a thumb and sucks it clean, shuddering.

“That wasn’t… too bad,” she says, her confident tone slightly belied by her still-trembling body. “Mommy could show you some more… but maybe someplace a little more… intimate?”

You put your trousers back on and tell her to follow you. Grabbing her by the hand, you lead her out of the alley and trace the familiar walk back to your place. It’s not a far walk, but knowing that more time spent with _her_ is waiting for you makes every step feel like it takes a lifetime. People eye the two of you, flushed and clutching each other’s hands, as you pass them, but you couldn’t care less. Your rental mommy still has more tricks up her sleeves, it seems, and you can’t wait to see what she has in store.

When you turn a corner and see your place in sight, you turn to tell Jessie, only to pause at what you see. She’s idly wiping a few beads of cum from her undershirt, licking her fingers clean. You feel your cock start to bulge again as she eyes you hungrily, and hurry her along.

Once you’re inside, you have just enough time to draw the blinds in your living room before Jessie sheds her top and undershirt. Her boobs are still glistening with cum and sweat, and she cups and plays with them, her face again growing flush. You unbuckle your pants and drop them, freeing your manhood once more, and she croons at the sight of it.

You ask her if she’s ready, and her reply electrifies you: “Mommy’s reader for whatever you want. Do _anything._ In fact…” She idly wipes more cum off her tits and sucks it. “Mommy likes it a little _rough._ ”

Nodding, you position yourself behind her and hold her close. You feel her naked back against your flesh, slick and warm, and you course your hands over her front, hearing her trill as you play with her rock-hard nipples and appreciating the way she shudders as you slip your hands into her panties. You whisper into her ear, telling her to prepare herself, before grabbing the back of her head.

You force Jessie to her hands and knees as she moans with delight, telling you to do it more, and then you hook a finger around her skirt and panties, yanking them down to her knees. Her glistening womanhood is there, flushed with arousal and open for you. Around it, your earlier suspicions are confirmed: her ass truly is enormous.

Grabbing handfuls of ass, you position yourself behind her, your cock lining up with her moist entrance. You savor the moment, just for a bit, and then push yourself into her.

Jessie’s breath escapes in a flurried gasp, and her voice sings out a long, keening moan. You hold your cock inside, relishing the sensation, and then begin pumping in and out, fucking her at a slow but steady pace.

“Harder,” she pants between thrusts. Her breaths are growing heavy as she pants from arousal. “F-fuck mommy harder! Do it!”

Obediently, you pick up the pace, rutting her over and over again, your massive cock spreading her open. Still holding on tight to her bountiful asscheeks, you grunt and slam in particularly hard, making her squeal as you hilt for the first time. Leaning forward, you push her head down into the ground. Jessie dutifully complies, her head pressed along the floor as she raises her waist to compensate, and you take the time to pick up the pace, fucking her without pause.

“Ahhn—a-ahnn—do it—nnnngh—d-do it harder—gggnh—harder! Fuck me harder!”

Her desperate cries ringing in your ears, you feel a surge of excitement and lust as you seek to satisfy her. Confidence brimming through your body, you keep hold of her head with one hand, keeping it pressed firmly into the ground, while the other retains its grip on her ass. All reservations dissolved, you ride her with everything you’ve got.

Your cock hammers into her over and over again, quickly growing slick with her fluids. Between thrusts, she continues to entreat you, and you resolve to fuck her so hard that the pleasure makes her unable to vocalize anything but cute little whimpers and cries.

As you hilt her over and over again, your pace continuing to pick up, you find yourself awash in ecstasy. Your vision haloes as the bliss washes over you, and you shudder. There’s a knot of pleasure in your groin which tells you that an orgasm is building. But you can’t cum yet—not until you’ve given this woman everything she needs.

Thankfully, Jessie seems to be more than enjoying herself. Every time that you hammer into her, her voice erupts in a grunt or a shout that warbles with appreciation. Before long, her voice soars through the living room in time with your own pounding thrusts: “Nngh—guh—hnngh—aagh—nn-guh!” Her face is flushed, and her tongue is lolling from her mouth. You come to realize that you can’t even begin to envision what she’s feeling. The delight that’s coursing through her body right now is increasingly reducing her to a quivering, moaning mess. Your repeated hiltings leave the sound of wet bodies slapping against each other filling the room. The sheer volume of the sound is surprising, as is its regularity. Is it really _you_ who’s doing this? Impressed by your own tenacity, you pick up the pace until you’re positively jackhammering into her, the incredibly fast pace both draining and yet somehow enticing. You don’t want to stop—not until you both cum.

And you’re getting close. That sensation at the base of your cock is growing, and you grunt as it starts cresting its way up. Your grip on her ass tightens as it builds and builds, grunting. You tell her you’re close, and she responds with a coo—one that’s interrupted with a squeal as you slam into her with particular force. She’s close too, you realize. It’s going to be a good one for both of you.

By now, Jessie’s composure is completely gone. She’s trembling with delight underneath you, and at one especially forceful thrust, her pussy clenches tight around your cock, milking you for all you’re worth. That proves to be the final tipping point—you gasp as you finally release, still holding a tight handful of her cheeks. Grunting, you push yourself as far in as you can, your cum surging out of you and filling her. The sensation is what pushes her over the edge as well. She cries out, her voice high and keening, as she herself orgasms, her pussy still clenching and milking you. Both of your orgasms crash at once, and you slump into her, panting, as she herself fights for breath.

Finally, regaining your pace, you slide out of her, the slow movement making her groan with delight. When you’re finally free of her, you flop back onto your back, still panting. It’s finally over.

Or so you thought.

Surprise blossoms through you as she crawls up to you, smirking, and takes your cock in her mouth. Her eyes flutter at the taste of your cum and hers, and she moans appreciatively around your rod before she begins sucking you off.

You grunt, panting, almost not knowing how to react. She’s still going? This woman is limitless!

Giving you no time for a break, she continues sucking you off, and before long your member is hardening again. Smirking at you, her eyes smoldering with lust, Jessie goes to town.

You gasp as her mouth moves up and down your shaft as she fellates you, expertly taking your cock and even bringing it to the back of her throat. You can’t help but be impressed at how well she does it.

Eying you, she moans sensually, and picks up the pace, lathering your shaft with her mouth and teasing the tip with her tongue. Before long you feel yet another orgasm coming your way.

But she suddenly slows down, sliding her mouth off of your member and grinning your way. “Oh, you’re coming close already?” she teases, casually wiping her chin. You grunt with need and ask her to continue. She laughs.

“Ohhh, but mommy isn’t ready for it to be finished just yet. She has needs too, you know?”

As she takes your cock in her mouth again, going slower this time, you reflect on how insatiable she must be, to babble on about her needs after you made her cum twice.

Jessie’s ministrations on your cock are those of an expert, and you lie back on the floor, your energy returning with stubborn slowness, as you are awash with bliss. Her hot and slick mouth is almost as good as her tunnel, and when she moans sensually around you, you can _feel_ the sound like a vibration, the sensation one that tickles your pleasure centers and sends bliss coursing through your body. You find your hands clenching and unclenching as you near the crest again—

And she stops. You look up, frustrated, as she eyes you wickedly. “Do you need it?” she teases. “Do you want it?” You mutter something snarky and her grin just widens. “Tell mommy you need it,” she croons. “No more games this time, promise, I’ll let you finish—but you have to tell mommy you need it.”

You tell her, and she looks delighted. “Well then…”

She goes down on you with renewed vigor, sucking away, and more and more pleasure washes through your body. At several points her lips make it all the way to the base of your cock as she takes the whole thing in, the heat of her mouth almost unbearable. Finally she bobs up and down, releasing a series of grunts, and you feel the wave of ecstasy approach you as the orgasm approaches—

You cum, finally, and gasp as your teased and denied cock is finally allowed to spend itself. Your shaft pulses as you pump seed into her, and her eyes widen at the sensation and she shudders before slurping it all up. She swallows as much as she can, even as your cock refuses to stop, and when you finally finish, sprawled in post-orgasmic delight, she gives one final slurp and finally lifts her head away. When she pulls it free, you notice there’s no cum to be found anywhere on your shaft, or around her mouth, either. She took it all, not wasting even a single drop.

You’re so spent that you are barely able to move yourself off the floor. You stagger your way up, first to your knees and then shakily to your feet, while Jessie watches with obvious amusement. “Why don’t you rest for a minute, big boy,” she teases. She walks over to her discarded bottom and panties and slides both back on—slowly, giving you one last look at her honeypot and bountiful ass before covering them up.

“That’s right, rest,” she continued, looking at you. “Mommy had a lot of fun—more than she’s had in a long, long time. She’s thinking she might want to go and bring a friend back.”

You start at that. She’s _still_ not done? But her hungry eyes and challenging smirk rouse you. Whatever lengths this woman can go to… you can meet them! You tell her that you’re ready.

She looks pleased. “Well then,” she says huskily, “you just wait here. Mommy’s going to go get her friend and be back in about an hour.” As she turns and walks away, you catch a slight hint of the black panties peeking over the top of her skirt. Even after getting to know Jessie intimately, the sight still excites you.

As your door slams, you settle back with a contented sigh. An hour, huh? You’ll have to try and recuperate before she returns with company. But you’re confident that you can handle anything she dishes out.


End file.
